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Diphenyl selenide, diphenyl selenoxide, diphenyl selenone compounds and uses thereof

A kind of technology of diphenylselenyl sulfoxide and diphenylselenide, which is applied in the field of medicine

Inactive Publication Date: 2013-05-08
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The study of diphenylselenide, diphenylselenoxide, diphenylselenone sulfone and their related compounds as tumor cell proliferation inhibitors and tumor blood vessel destroyers has not been reported so far.

Method used

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  • Diphenyl selenide, diphenyl selenoxide, diphenyl selenone compounds and uses thereof
  • Diphenyl selenide, diphenyl selenoxide, diphenyl selenone compounds and uses thereof
  • Diphenyl selenide, diphenyl selenoxide, diphenyl selenone compounds and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] Example 1: Preparation of 3, 4, 5-trimethoxyphenyl-4-methylphenylselenide (compound 1)

[0127] 1 g of 3, 4, 5-trimethoxydiselenide was dissolved in anhydrous THF, and 0.77 g of lithium aluminum tetrahydrogen was added to react for 1 hour to obtain 3, 4, 5-trimethoxydiselenol. Add 0.25 g of p-methoxyaniline to another reaction flask, add 0.5 ml of concentrated hydrochloric acid, stir to dissolve, add 0.14 g of sodium nitrite at 0 degrees Celsius, and react for 30 minutes. Afterwards, 30 ml of water and 3 g of potassium carbonate were added to the prepared benzoselenol solution at 0 degrees Celsius, and the prepared diazonium salt solution was slowly added dropwise at 0 degrees Celsius. After the dropwise addition was completed, the reaction was carried out for 2 hours. Afterwards, the reaction solution was acidified and extracted with ethyl acetate, the organic layer was washed with saturated aqueous sodium chloride solution, the organic layer was separated and dried...

Embodiment 2

[0128] Example 2: Preparation of bis-3, 4, 5-trimethoxyphenyl selenide (compound 2)

[0129] Compound 2 was prepared in the same manner as in Example 1 except that corresponding raw materials were used, and the yield was 80%. ESI m / z 437.1[M+Na] +

Embodiment 3

[0130] Example 3: Preparation of 3, 4, 5-trimethoxyphenyl-p-chlorophenyl selenide (compound 3)

[0131] Compound 3 was prepared in the same manner as in Example 1 except that the corresponding raw materials were used, and the yield was 86%. 1 H-NMR (300M, CDCl 3 ), δ7.33(2H, d, J=8.62), 7.23(2H, d, J=8.62), 6.74(2H, s), 3.85(3H, s), 3.81(6H, s), ESI m / z 359.2[M+H] + , 381.2[M+Na] + .

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Abstract

The invention belongs to the technical field of medicine, and relates to diphenyl selenide, diphenyl selenoxide, diphenyl selenone compounds and related compounds thereof, wherein the structure is represented by the following formula. The present invention further provides pharmaceutically acceptable non-toxic salts and hydrates formed by the compounds represented by the structure formula, wherein the pharmaceutically acceptable non-toxic salts comprise salts formed by the derivatives and acids or bases. Pharmacological activity experiment results show that the derivatives have good tumor inhibition activity, and can be used as tumor cell proliferation inhibitors and tumor vascular disrupting agents to be used for antitumor drug preparation.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a kind of diphenylselenide, diphenylselenone sulfoxide, diphenylselenone sulfone compounds and their application, more precisely, relates to the compound and its function as tumor cell proliferation inhibitor and tumor blood vessel The application of the destructive agent in the preparation of anti-tumor medicaments. Background technique [0002] Malignant tumor is a serious disease that threatens human health and life, and it is the leading cause of death in China. Searching for and discovering new drugs for the treatment and prevention of tumors is a major issue at present. [0003] Combretastatin A-4 (CA-4) is a cis-stilbene natural product isolated from South African willow, and its chemical name is ( Z )-2-methoxy-5-(3,4,5-trimethoxystyryl)phenol. CA-4 is an inhibitor of tubulin polymerization, which exhibits a strong inhibitory activity on tumor cell proliferation and tum...

Claims

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Application Information

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IPC IPC(8): C07C391/02A61P35/00
CPCY02P20/55
Inventor 张为革沈杞容吴英良高训英姚飞王金红文志勇乔佛晓孙俊齐欢
Owner SHENYANG PHARMA UNIVERSITY
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